Hydrochloric Acid → HCID 13669838, compound

HRID 1194850Notes

Reaction equation

HRID 1194850 reaction equation
[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].Cl>O.CN(C=O)C>[Cl:1][C:2]1[C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([Cl:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:26][C:27]([OH:29])=[O:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 15617006HCID 15617006, compound

Product 1

HCID 13669838HCID 13669838, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,7-dichloro-3-hydroxy-9-oxo-9H-xanthene (2.0 g), potassium carbonate (3.4 g), ethyl bromoacetate (4.2 g) and DMF (60 ml) was stirred at 60°-65° C. for 4 hours. After cooling the mixture, sodium hydroxide (4 g) and water (100 ml) were added and the resulting mixture was stirred at 90°-100° C. for 30 minutes. After cooling, the mixture was rendered acidic with hydrochloric acid and the solid crystal was recovered by filtration, washed with water and dried. Recrystallization from DMF gave 1.3 g of 4,7-dichloro-9-oxo-9H-xanthene-3-yloxyacetic acid. m.p. 262°-263° C. This compound gave a mass spectrum having a molecular ion peak at m/e 338.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred at 90°-100° C. for 30 minutes
  3. temperatureAfter cooling
  4. filtrationthe solid crystal was recovered by filtration
  5. washwashed with water
  6. customdried
  7. customRecrystallization from DMF

Sources & evidence

ORD record
ord-a04cf948029e4baeacd51ae1e9c127bc
Source dataset
uspto-grants-1989_03
Patent number
US04816479

Reaction notes

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